Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 54249396, compound

HRID 1420704Notes

Reaction equation

HRID 1420704 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][C@H:15]([CH3:24])[CH2:16][O:17]C3CCCCO3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C(O)C>[CH:10]1[C:11]2[N:12]([CH2:14][C@H:15]([CH3:24])[CH2:16][OH:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57257503HCID 57257503, compound

Product 1

HCID 54249396HCID 54249396, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Compound 9 (0.47 g, 0.0145 mol) was mixed with pyridinium-4-toluene-sulfonate (PPTs) (0.037 g, 0.15 mmol) in ethanol (20 mL). The resulting mixture was stirred at 50° C. for 24 h. The solvent was evaporated in vacuo. Purification of the crude product on a silica gel column (Eluent: ethyl acetate/n-heptane (1:1)) gave the title compound 0.226 g (65%) as a solid. M.p. 80-81° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customPurification of the crude product on a silica gel column (Eluent: ethyl acetate/n-heptane (1:1))

Sources & evidence

ORD record
ord-663351808a9e4a37a0fe517bbc92d800
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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